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R3.3 Electron sharing reactions

Understanding Points
Reactivity 3.3.1—A radical is a molecular entity that has an unpaired electron. Radicals are highly reactive.
Reactivity 3.3.2—Radicals are produced by homolytic fission, e.g. of halogens, in the presence of
ultraviolet (UV) light or heat.
Reactivity 3.3.3—Radicals take part in substitution reactions with alkanes, producing a mixture of
products.
Radical: a chemical entity with an unpaired electron
e.g. Cl⦁, ⦁CH3, ⦁OH
Due to their high reactivity, radicals are usually formed as intermediates in a reaction
Bond breakage
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Heterolytic fission
Homolytic fission
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Both electrons go to one atom, forming a cation and an anion Curly arrow depicts the movement of 2 e-
Each atom retains one electron, forming 2 free radicals Fishhook arrow depicts the movement of 1 e-
https://lh7-us.googleusercontent.com/k0Z2aHpk6hpmWg78QyO5VVBSitHGI9p9iCbr2baBqvFzS9cWnZbMxMA9iQ6rQ9Fu78nkHKiz8-3BkC3NoA7iebWzB4Wqrfzy8-IWMifilM8vbU1ea214tkTXbndrqwyfDCY6vPOvpoTsJ4R-ZC_8cpw
https://lh7-us.googleusercontent.com/b-CFStByf9sbGneE8zEBO_nt1RL-6_mBaoiwMIoOmIkrC_d7MxjEC14kVzVN1GWXzxdrcYSHSEOS_tHAwYxXeYkHbn2n5CJ8524wUjnKCeZ59Y3lio7G8mV9tSiY-C_Lj-b-tRHiOKzmTJQG4ZvLiWE
https://lh7-us.googleusercontent.com/-pEMplBZN_8lY5o7wh8co3nOp11Xhk7T4z3kVUww1ehpyhRUh4rw_LlnOUDUnPNRIeeBV8jTv4jF87Bl0D9BAvnqMMJFBhJi9HzI3Yx3VeSw2FJ6ra5peKqenBYO4wbf0LofZZfC4UeCcp7hisD8weo
Substitution reactions of alkanes
Alkanes undergo substitution with halogens in UV light
e.g. CH4 + 4Cl → CCl4 + 4HCl
1.
Initiation: radicals produced by homolytic cleavage of bond
1.
Propagation: new radicals produced
CH4 + Cl⦁ → ⦁CH3 + Cl⦁
⦁CH3 + Cl2 → CH3Cl + Cl⦁
1.
Termination: radicals react together to form a non-radical product
⦁Cl + ⦁Cl → Cl2
⦁CH3 + ⦁Cl → CH3Cl
⦁CH3 + ⦁CH3 → C2H6